


It's Complicated

by Denois



Category: Check Please! (Webcomic)
Genre: Alternate Universe, Friends With Benefits, Getting Together, M/M, Shitty is extremely "rich bro" in this, like there are extenuating circumstances making him more bro than usual, they are fuck buddies at first and there's allusions to that but no smut on page
Language: English
Status: Completed
Published: 2020-12-03
Updated: 2020-12-03
Packaged: 2021-03-09 21:06:49
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 9,879
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27853054
Author URL: https://archiveofourown.org/users/Denois/pseuds/Denois
Summary: After moving to NYC, Will doesn't have a lot of luck finding queer community, his friends and sister suspect that's because he doesn't go anywhere but work and home. They suggest giving dating apps a try.Derek has a deadline and three loud and annoying friends. Giving them free access to his phone and the dating apps on it to get them to leave him alone was probably not his smartest move, but it did work. Mostly. Besides, even if they do find a hookup for him, it's not like he's going to fall for the person, right?
Relationships: Derek "Nursey" Nurse/William "Dex" Poindexter
Comments: 26
Kudos: 137





	1. Chapter 1

**Author's Note:**

> First of all, shout out to Enabler of the Year [Draskireis](https://archiveofourown.org/users/draskireis) for beta reading and enabling the creation of this fic while also enabling my Nanowrimo progress.
> 
> Second of all, this is largely the fault of [Pretty-Meris](https://pretty-meris.tumblr.com/) due to reblogging [this post](https://pretty-meris.tumblr.com/post/634260179020562432) and then enabling me about making it happen.
> 
> At some point, [this post](https://stimman4000.tumblr.com/post/628754234374078464/be-me-guy-whose-profile-says-hes-22-hits-me-up) also got added to the mix. 
> 
> This was supposed to be a short quick one shot....

> Vicky: How's life in the big city, lil bro? Met any cute guys yet?

> Will: It's fine. It's. There's 8 million people in the city and I talk to maybe 8. 

> Vicky: are they cute guys, tho

> Will: No. Well, one is.

> Vicky: Get it.

> Will: his girlfriend already "got it"

> Vicky: Damn

> Will: It's weird. With Uncle Sonny's bar, I never had to worry about finding like community and shit. I don't even know where to look here.

> Vicky: There's 8 million people, there's gotta be places.

> Will: Where?

> Vicky: IDK. I don't live there. Try tinder or grindr

> Will: I don't want to hook up. I want... I just want people.

> Vicky: So, say you want to date. People do that.

> Vicky: just download the app and try.

Will did download the app. Both of them actually. He even got as far as setting up his profile and uploading some pictures. And then he started looking through whatever profiles were popped up for him and they were all, _all_ , looking for hook ups.

Sighing, he tossed his phone on the other side of the bed. He didn't delete the apps, but he also wasn't planning on using them. He'd meet some queer people eventually. There were eight million people in the city, he had to meet some eventually.

* * *

"Brah. You know what your problem is?"

Derek didn't look up at Shitty's question. He'd explained to them all multiple times that he did actually have a deadline and that, ch'yeah, he could ask his publisher to push it back, but then he'd get a reputation for being difficult to work with. Then no one would want to publish him. And he wasn't going vanity press. So he was only half listening to what his friends were talking about and mostly trying to figure out how to make the meter on his poem work.

"Your problem, brah, is that you need to get laid. Get your dick wet and the words will flow."

When Shitty's hand landed on his shoulder, Derek did look up with a deep breath. Chill, like, on one hand, yeah, it had been awhile since he got laid. On the other....

"I'm not sure I want to take advice about mixing sex and poetry from a guy named Byron."

"Harsh, bro. He can't help who he's named after." Adam wasn't even in the study where Derek was writing. His voice just boomed in from the next room over.

"Chill. I'm not going to try to find a hook up while I've got a deadline on my first draft."

Justin had apparently joined Shitty in the room because it was his hand that reached out and swiped Derek’s phone off the desk. "No worries, bro. We got your back. You got a grindr or tinder?"

"No. I've got a deadline."

"Even better. We'll set you up and find you a hottie to bang. "

"And then the words will flow, my brah."

"You know what. Whatever. Chill. Just, let me write."

In retrospect, Derek probably should have been a lot more worried about how quiet the three of them got in his den, but at the time, he was mostly concerned with finally finding the perfect phrase and moving on to the next line.

* * *

“Wait, you aren’t serious, are you?” Chris was looking at him with his mouth open in shock. 

“It’s no big deal.” Will didn’t really want to talk about it, so he grabbed the plates and headed for the kitchen to rinse them off.

Chris and Cait weren’t willing to let it go and followed him, leaning against the counters with arms crossed. 

“Seriously. It’s not ok, Will.”

“Why would it not be ok?”

“Because cooking for your neighbors shouldn’t be the highlight of your week, dude?” Chris’s wide gestures nearly knocked the plate out of Will’s hands, but he managed to save it.

“You’re my friends. I like cooking. I like hanging out with you. Why shouldn’t that be a good time?” He turned off the water and turned to look at them. Apparently, they were having this discussion whether he wanted to or not.

“It’s hella swawesome that it’s a good time. But it shouldn’t be the highlight of your week!”

Cait was much more subdued as she gently lay a hand on his arm. “When you moved in, you were asking about queer community stuff and wanting to meet people and date. We just wonder why the highlight of your week isn’t going on awesome dates.”

“Well, for starters, you two turned me down.” Will tried a grin, but they didn’t look like they were buying it.

“Did you just give up? Decided to settle for a weekly hangout session?”

The problem was that they actually cared. They wanted him to be happy and he was. He was happy. They were great friends and he loved hanging out with them. He was pretty sure that dating random guys wouldn’t be better than their weekly hangout. 

“I didn’t give up. I downloaded tinder and grindr. No luck, so I just figured, if it happens then it’ll happen organically.”

“Organically? When you don’t go anywhere except work, the wood shop, Lowe’s, and here?”

“I could meet someone at Lowe’s or the wood shop.”

Cait snorted. “Ch’yeah. But you aren’t looking for lesbians.”

“Why didn’t tinder and grindr work?”

Will shrugged again and looked away. “I’m not the right kind of gay.”

“There’s no way to not be the right kind of gay.”

“Tell that to the people who sent me messages saying they were going to report me for being straight and trying to commit hate crimes, ok?”

He pushed past them and back out to the den area. This is what he didn’t want to talk about. This was why it was always better to just let things happen if they happened. And if they never happened then it was fine. Good friends were just as hard to find and just as important as a boyfriend. 

They followed him out. It’s not like they wouldn’t. They were in his apartment. 

“Will. Why would anyone assume that about you?”

He waved his hand vaguely. “The Ryan Lochte stuff in Rio or whatever. I guess that I just give off the vibe. Like too many straight guy things.” He sighed and sunk into a chair. “It’s fine. It’ll happen if it happens and if not, I’ve still got great friends.”

“Will, if you really don’t want to give the apps another try, or finding a queer community group or something, we’ll let this drop. But if you are just trying to avoid a few jerks, then Chris and I can screen your matches and messages for you.”

“You don’t have to do that.”

“No, no. We want to do that.”

“It’s true, she loves swiping for people. She’s hella good at finding good matches, too.”

Shaking his head, he tossed his phone over to them. “Fine. Can we watch the movie now?”

* * *

“Hey, Derek. Derrino. The Derester.”

“What, Shitty?”

“Does your dad still have that standing reservation for a suite at The Mark for business clients or whatever?”

Derek looked up from his laptop, brow furrowed in confusion about what that had to do with anything. “Uh, probably.”

“Swawesome.” Shitty leaned over and yelled into the other room. “Tell ‘im he’ll send a lyft to take him to The Mark.”

“Who-wha-why? You can’t use my dad’s business suite to get laid, Shits.”

“Not me, my poetical pal. This is for you.”

“I’m not using my dad’s business suite to get laid, Shits.”

“Sure you are. We discussed it, remember? Justin found a nice ginger hottie and we’ve chatted him up for you. Personally, I think he’s a tad masc for masc, you know, but Adam and Justin are pretty committed that he’s the best option tonight. Now, all you need to do is go to The Mark, get laid, and the words will appear.”

Derek resisted the urge to massage his temples. “That’s not how it works. The dick is not the key to the word vault.”

“Won’t know until you try. But if it doesn’t work, I’ve got some weed that definitely will.”

“I was serious. I’m not using my dad’s business suite for sex. I don’t even know for sure he doesn’t already have a client using it. Or a mistress. Whatever.”

Shitty had the audacity to look astonished by the possibility that the suite might not be available for his last minute schemes. “Then you better hurry up and reserve another suite because Adam is definitely sending a lyft to take this guy to The Mark.”

With a sigh, he saved his document. Then saved it again. Then saved it a third time. He really didn’t want to admit defeat, but it was the easiest way to get them to leave him alone. Probably the guy would just not show or would leave and he could get some work done in the peace and quiet of the suite. It was a small price to pay.


	2. Chapter 2

“Oh, hella cool.” Cait leaned forward and turned off the tv. Which was kind of rude because the movie wasn’t over yet. “Will, you’ve gotta go get dressed.”

“I am dressed.” He looked down at himself. Just as he remembered, jeans, tshirt, flannel, boots. He could even feel the socks on his toes. Definitely dressed.

“No. Like, get dressed for a date.”

“Um. No.” He reached for the clicker to turn the tv back on, but she swatted his hand away.

“Yes. You matched with this guy, he’s super hot, smart, rich apparently. A little bro-ey in messages, but whatever, it’s a date not an engagement.”

Will raised an eyebrow at her. “So?”

“So, he’s sending a lyft to take you to The Mark so you can meet up.”

He leaned back in the chair and rolled his eyes. Then rolled them again. “You mean hook up. And there’s no way someone’s trying to hook up with me at The Mark. Probably an organ trafficking scheme or something.”

She held his phone out to him and wiggled it until he took it and looked at the profile that was open. The profile definitely featured a hot guy. Wicked hot. And all the info provided was interesting, kinda funny, kinda dorky. 

Then he tapped for the message history and fixed her with another raised eyebrow look. 

“Yeah yeah. But he promised a ride in a helicopter. Even if he’s a rich jerk, how many offers of a free helicopter ride are you going to get?”

“What if I don’t care about taking a ride in a helicopter?” 

She made a face. “Except you definitely do, because he agreed to you bringing friends for a double helicopter date.”

Will couldn’t help but laugh at that. “Oh, so you want me to date this guy just because _you_ want to ride in a helicopter.”

“Well, yeah. I thought that was hella obvious. But also his texting style changes, so I think maybe he has a friend messaging for him, too. Could be he’s not so… bro.”

“Could be this is an organ harvesting plot. There’s at least a 93% chance that if I get in a lyft he sends me that I’m going to get wicked murdered.”

“So, you’ll do it?”

He sighed. “With odds like those, why not?”

* * *

Derek was finally getting to relax in the suite at The Mark. Well, as much relaxing as he could do while still worried about his looming deadline. Still, it had a well stocked wet bar and room service. And most importantly, a distinct lack of his friends. He wanted to be supportive of Shitty, he really did. That’s why he’d let him crash at his place. It was why he’d invited Adam and Justin over. But he seriously couldn’t miss this deadline and Shitty didn’t seem to understand that at all.

But still, he was alone and he could focus and he could take actual self care breaks to recenter himself. 

And there was a knock at the door. 

He was tempted not to open it. He hadn’t ordered room service yet, it was way too late for housekeeping, and after reading what his so called friends had sent the, admittedly very hot, guy that they’d matched with, he was pretty sure he’d never manage to hook up with the dude ever. 

Still, there was a chance it wouldn’t be a wrong room and it _could_ be something important, so he answered the door.

Immediately, he had to swallow hard and couldn’t stop himself from licking his lips as his eyes darted down the body of the man in front of him, and back up to his eyes. One ginger eyebrow was raised.

“Chill. You actually came.”

At that the guy frowned, not like he was upset, but like he was confused and trying to work out a pun or riddle or something. 

“You invited me, man. If you want me to leave, I can go. Could have saved me time and bus fare by just swiping the other way, though.”

“No, that’s not what-.” He shook his head and stepped back. “Do you want to come in?”

The guy (Will? Was his name Will? Derek couldn’t remember what the profile on his app had said) raised an eyebrow as he followed Derek into the suite. “Pretty sure that’s why I’m here. So, why didn’t you expect me after sending a lyft for me? Why get a wicked fancy suite if you didn’t expect me to show?”

“For the same reason, actually.” He dropped onto the couch in the main den area of the suite and gestured for the other man to sit wherever. “My friend, Shitty-”

“Your friend Shitty?” The guy hadn’t taken the seat next to him on the couch, but he also wasn’t across the room or something, and he had sat down, so it was fine. 

“Ch’yeah. That’s a nickname. His real name’s Byron, which is a pretty shitty name, plus his initials are BS, so.”

“Ayuh. Got it.”

“Yup. So Shitty’s been having a rough time lately with his dad. Threats of disinheritance, cutting off financial support, general asshattery, the usual kind of stuff.” 

“Sure. Dads.”

“Exactly. And all because Shits said that he didn’t want to be in house counsel for his dad’s company and wanted to do activism law.”

The guy nodded. “I can understand now why you didn’t think I’d show up.”

Derek rolled his eyes. “I’m getting there. Anyway, Shits is kicked out of his family’s house and cut off and not sure if his grandparents or anyone is gonna back him or if he’s really just on the street just like that. So, he’s staying at my place, but he’s-” Derek broke off and puffed his cheeks up with air before letting it out slowly. “He’s loud and needs a lot of attention. Which is usually chill because I can roll with it, you know? But I’ve got a deadline from my publisher and I don’t want to ask for an extension and I can’t work like that.” 

He had to stop and take another breath. Then another. He’d forgotten to breathe for a minute there. “Yeah, so. I invited a couple of college friends over to chill with him and they were still bugging, insisted I needed to get laid, so I was like, whatever, swipe for me. Then apparently they set up this hook up, and I was like, whatever, right? It’s chill. You’re hot. When I read through the messages, I figured you probably wouldn’t show, but at least I could get some work done in the suite. But I guess you are really into rich guys who are flashy about it.”

The dude leaned back in his chair, regarding him for a long moment. “So, you didn’t even swipe right on me. Your friends did.” 

“Like I said, it’s chill. You’re hot. I probably would have anyway.” 

The eyebrow raised again.

“Maybe.”

“Ayuh. That’s what I thought. I’ll have to tell Cait she was right.”

It was his turn to be confused. “Cait?”

“My friend who was swiping for me. She said maybe you weren’t such a-. You know what? Not important. She just figured that you might have had friends messaging for you and said I shouldn’t judge by the messages.”

“Seriously? Are you serious right now? After you just tried to make me feel bad about not being the one to swipe right on you, you didn’t even swipe right for me?”

The guy was smiling now. “Oh, it’s worse than that. She wanted me to accept your invite so she and her boyfriend could go on a double date with us on the helicopter ride your friends promised.”

“Wait, no. Back up. Did you really come here to hook up with me just because your _friend_ pressured you to do it?”

The guy met his gaze for a long moment then looked away with a sigh. “No. I came here because my friends were right that I’d given up on finding any kind of community or potential dates or whatever. I liked your profile. You’re wicked hot. And I don’t usually do casual stuff and hookups, but whatever. How many chances am I gonna get to fuck The Man?”

“Well, I am tha man, that’s true. But seriously, dude. I can get you a lyft back or something if you don’t want to do this.” 

“It’s whatever.” He took another breath and then looked up to meet Derek’s gaze again. “The difference is, I would have swiped right for you. But,” he paused and lifted one shoulder in a shrug, “you haven’t killed me or stolen my kidneys yet, so it’s going a lot better than I actually thought it would. The messages from your friends had me pretty convinced that the best case scenario getting into that lyft was I’d meet the most irritating asshole of a rich person possible. You’ve, uh, you’ve exceeded expectations.”

“FWIW-”

“Did you just say ‘FWIW’?”

“FWIW, I’m glad my friends swiped right on you for me. And I’m glad I didn’t take their advice and leave a few grand laying around on a table or something.”

“That sounds like a quick way to get robbed.”

“Ch’yeah. They, they might have been drinking? Or high. Or both.” Anyway. In case you missed it on the profile, I’m Derek.”

“Ayuh. I recall. I’m Will. In case you missed that.”

He made a face and blew air out between his lips while waving off the suggestion. “Pssh. I knew that.”

The very corner of Will’s mouth lifted in a smile. “Well, you’ve got a deadline, so I’ll, uh, not take up any more of your time. Just, like. If you were serious, message me again if you want to hang out. Doesn’t have to be a hookup.”

“Chill. You know, if you wanted to stay, I am allowed self care breaks.”

“Are you now?”

“Ch’yeah. They’re mad important.”

“I bet.”

Will was smirking, but when Derek stood up and walked over to drop into his lap, he didn’t move away. No, he reached out and wrapped his arms around Derek to anchor him there. 

Self care was mad important.


	3. Chapter 3

> Derek: Hey, wanna come over? [eggplant emoji]

> Will: Can’t. Tonight’s friend night with Chris and Cait.

> Derek: Srsly?

> Will: Ayuh. Cook for them every week.

> Derek: We’re friends. With benefits. Still friends

> Will: You can come over if you want. But it’s homemade dinner and a movie.

> Derek: ….

> Derek: You could come over tomorrow?

> Will: It’s a date

> Derek: I’ll send a lyft 

> Derek: [winky face emoji] [eggplant emoji] [peach emoji]

Will rolled his eyes and locked his phone. It had been a few weeks since he met Derek and he still wasn’t really sure what was going on between them. Every so often, Derek would send him a message like that, asking to meet up. Usually it was at one high end hotel or another. Places Will hadn’t ever really considered entering, much less staying in. Even if it was only for a night, or even less, a few hours. 

Multiple times a day, however, Derek would send him memes and pictures and jokes. It had gotten to the point where he had to disable notifications while he was at work to avoid the temptation of checking. But it was just a casual thing between them. They talked a little before or after they hooked up when Derek invited him to whatever hotel. They sometimes talked about the things Derek sent him during the day. 

But they hadn’t really had any substantial conversations. He knew Derek had a publishing deadline, but he didn’t even know what kind of an author Derek was or if he preferred coffee or tea or hot chocolate. Those weren’t the kinds of things you just asked. Either Derek would open up to him, or he’d learn it over time. Or he could face facts and acknowledge the fact that it was just a casual relationship that didn’t really mean anything to Derek. 

Whatever, it wasn’t like he expected them to end up married. He just wasn’t used to casual. And it didn’t help that for all of Derek’s edges, he kind of wanted to be Derek’s friend, too. Maybe he should float the idea about Derek joining them for friend night again. Except he’d do it ahead of time so Derek could check his schedule.

* * *

The car stopped in front of a row of brownstones. Not the sort that had been subdivided into middle class apartments. If any of these _had_ been divided into apartments, they were well _well_ above his pay grade. 

“This is it.”

Will looked at the driver who was waiting somewhat impatiently. “There must be a mistake.”

“This is the address on the request, man. If you want me to take you somewhere else, you can put it in, but it’ll be more.”

Will rubbed his head. “No. If this is where it said. This is fine. Thank you.” 

He offered the guy a tip and climbed out of the car to stare at the building in front of him. 

Worst case, he-. Okay, worst case, someone thought he was there to rob one of these places and called the cops on him. More likely not-great case, he was in the wrong place and he’d just have to pay for his own lyft to get home or figure out where he could get a bus.

He pulled out his phone and messaged Derek.

He did not get a reply, instead the door opened and Derek gave him a saucy wave and smirk. 

Once they were inside, he was surprised to see that it looked like the place was pretty lived in. “Where are we?”

“My house?”

“Oh. Oh my goodness. Look at you. Aren’t you just the most beautiful thing? May I pet you? Thank you.” He hadn’t meant to get distracted, but there was a giant, beautiful, orange Maine Coon laying on the couch.

From the way the cat was laying, it was clear she owned the place and only deigned to allow Derek to stay there, so it was really only proper that Will pay respects to her first. She accepted a few pets and some scratches between the ears with a low rumbly purr and rubbed her head against his hand. He might be in love. 

He really shouldn’t fall in love with his… hookup’s cat. 

“I can’t believe she’s letting you pet her. She’s been hiding the entire time my friends were staying over. She hates people.”

Will gave her one last scratch and stood up from where he’d dropped beside her. “Hmm. Maybe she’s just got good taste. Your house, huh? Where, uh, where do you want to do this?”

Derek’s smile broadened into a grin and led him into a bedroom. As soon as they were in the room, Will moved into his space to pin him against the wall and press heated kisses to his mouth and jaw. 

It’s how they worked, apparently. That wouldn’t change just because they were at Derek’s house.

Later, after, Will stretched as he walked across the room to the ensuite bathroom, making his spine pop. He had his doubts about this being the actual master bedroom. This looked like the kind of place that had ensuites for all the bedrooms, and it’s not like Derek would take all of his hookups and casual datemates into his personal space. But it didn’t matter. As long as there was an ensuite with actual washcloths and a trash can. He could get cleaned up and clean up Derek. 

Derek was still stretched out on the bed, watching him lazily when he was finished. 

“Do you want to tell me where the kitchen is, or just let me wander around your house by myself?”

“Why? You could just stay here.” 

“Because you should really drink some water and since we aren’t at a hotel, I’m not sure where the bottled water is, or even any glasses.”

At that Derek lifted himself onto his forearms and gave Will a considering look. “Why do you do this?”

It was a wicked weird question to ask. He was pretty sure Derek knew why he did this. “It’s a mutually beneficial arrangement, right? Unless you aren’t enjoying it.”

“Chill. I enjoy it a lot. But I meant this.” He waved his hand around in a way that didn’t clarify anything. “The washrag and the water and stuff.”

He paused and took a deep breath. “Dried lube is wicked itchy, and if I’m going to fuck your brains out, the least I can do is make sure you don’t dehydrate after, right?”

“Ah.”

“It’s just part of the deal. It’s, uh, chill.” 

“Right. Kitchen is back down the hall and then the door on the far left.”

* * *

It was the smell that convinced Derek to get out of his bed. These days it was always the smell. The wonderful aroma of homemade food. He really wasn’t sure how Will had managed to make anything edible the first few times he’d decided to cook for Derek. Mostly because Derek didn’t keep a lot of ingredients in the house, preferring to order takeout be delivered to his door. But it had become routine, and it was, it was nice.

He must have been quieter than usual padding toward the kitchen, because he managed to catch Will talking to The Contessa.

“You can’t have any of that part because it’s got onions and garlic and things not good for kitties. But a tiny bit of the meat won’t hurt.”

He was holding his hand out in front of her and she leaned her fluffy head down to literally eat out of his hand. Then, to Derek’s surprise, he crouched down so that she could jump up onto his shoulders before moving back over to finish cooking.

Derek covered his mouth to avoid making a noise and backed away slowly. He’d known that The Contessa was smitten; she followed Will around and rubbed against his legs constantly while she refused to be in the same room as most of Derek’s other friends.

It had been going on for weeks, months even at this point. And honestly, eventually Derek was going to have to admit it. Will was good with his cat. She loved him. And Derek thought he might be starting to love him a little bit too. 

Posting to reddit on his phone, of all things, might not have been his smartest move, but he really needed some insight. He had to be overreacting right? 

Just because Will was good with his cat didn’t mean he should develop feelings for him. 

Just because Will was an amazing cook who was making his stomach growl didn’t mean he should fall for him. 

Just because Will constantly and consistently showed tenderness and care which he brushed off as not worthy of noting didn’t mean he should _love_ him.

For one thing, he should definitely have considered the fact that he liked him as more than a hookup at some point before he started thinking about long term relationship potential.

He posted the thread and headed back to the kitchen. “Smells delicious. Are you going to stay and eat this time?”

As usual, Will gave him a half laugh and a half of a smile. “I’m okay. I get to eat before things get heavy.” 

Then he followed that with a smirk instead of the soft half smile which made Derek roll his eyes.

“Actually, I wanted to talk to you. If that’s chill.”

“Oh, ok. If it’s about me asking you to friend night, it really wasn’t a big deal. I wasn’t trying to push you. I mean, I know. Like you said, you wouldn’t have swiped right. I get it.”

Fuck, he had said that. He tried to make a mental note to thank Shitty and Adam and Justin at some point. Or at least whichever of them had done the actual swiping. The rest had nearly ruined it with the messaging. 

“No. I wanted to tell you that it’ll be a few weeks before I message you again for, you know, this. But it’s just because I’ll be in Europe for a book tour.”

Will seemed to get stiller, and maybe smaller, as he nodded slowly. “Right. Got it. Thanks for the warning. You should have a wicked great time. Be safe with whoever.”

“Wait, what?”

Will looked away and made a motion with his head that somehow conveyed “whatever”. “It’s fine. Chill, right? We’re not like, exclusive hookups. Kind of an oxymoron. It was clear from the start. Have fun in Europe.”

“Don’t slut shame.”

That got Will to look back over, his face furrowed with confusion. “I’m not? I’m seriously saying that I want you to be happy and have fun?”

“Chill. Well, that’s not-. You know what. Starting over. I’m going to Europe for a while, and I was wondering if you would check in on The Contessa while I’m away.”

“What?”

Derek thought back over his question. It seemed pretty straight forward. “She likes you. You can stay here, too, if you want. But, I thought she’d prefer if you were the one to check on her. I have a key for you.”

Will blinked slowly. “How do you know I won’t rob you?”

“Kind of a long con just to steal my belongings. I _would_ have to track you down to get The Contessa back though. She’s my baby.”

At that Will smiled. “Ayuh. She’s a sweetheart, even for a Maine Coon.” He ran his hand through his hair and then shook his head once. “Ok, fine. I’ll do it.”


	4. Chapter 4

It was weird, being at Derek’s house without him there. The Contessa was wonderful, of course. As a Maine Coon it was physically impossible for her to not be wonderful. She spent a lot of time curled up on or against him and purring, which was really nice. 

He wasn’t going to snoop through Derek’s things, so he stuck with sleeping in the room they always used for hookups and spent any other time in the rooms that Derek had shown him. Which was pretty much the kitchen and breakfast area, the den where The Contessa liked to sleep, and Derek’s study. If Derek had any houseplants that needed to be watered, he should have spoken up when he asked Will to cat sit. 

He also wasn’t going to invite people over to someone else’s house, so he returned to his apartment once a week for friend’s night with Chris and Cait. It also gave him a chance to do laundry and trade out clothes and stuff. 

Mostly things were just weird.

Weird.

Derek wasn’t messaging him multiple times a day anymore. He’d message once a day to check on The Contessa, but that was all. No memes. No jokes. He was in Europe, so normally Will would think that was the reason, but he was pretty sure that Derek wasn’t worried about international roaming charges.

Weird.

He was probably just busy. He was doing a book tour through multiple countries, and probably a dick tour as well. And it wasn’t really any of Will’s business. 

Except that it was weird to be sitting in Derek’s house, sleeping in one of Derek’s guest rooms, trying not to think about who Derek was sending jokes and memes to in Europe.

He scratched The Contessa’s head and cheeks. “It’s weird.” 

She just purred in response. She didn’t seem to find it very weird that Derek was gone.

“Things’ll probably change when he’s back.”

She started kneading her giant paws against his leg, stabbing him with sharp claws as she did.

“How long did I expect a casual relationship between someone like him and someone like me to last, anyway?” He leaned back and closed his eyes with a sigh, absentmindedly continuing the scratches and pets. “Not this long. Guys like him don’t hook up with guys like me more than once, maybe twice. If that.”

Apparently, he wasn’t doing a good enough job of giving her attention, because The Contessa stood up and moved onto his lap completely, then managed to put all of her considerable weight into her front paws as she placed them on his stomach.

“Oof. Come on, beautiful. Let me keep my spleen.” He stroked down her back and carefully eased her legs until she lay down with her weight more evenly distributed. “I will miss you. And the jokes and stuff. I’ll miss-. Nevermind. It’s weird.”

People didn’t have ex-hookups over to cook and chat and play with their cat. It would be weird.

It would be… pretty great.

* * *

Derek had avoided messaging Will since he got to Europe except to check on The Contessa. He’d brushed it off at the time, but it still sort of rankled that Will had insinuated that he was planning to fuck his way through Europe. Chill, like, what had he done to give Will that impression? He hadn’t even been the one to swipe on Will! 

He didn’t-. Okay. Chill. That wasn’t true. He did have casual hookups and flings. But not all the time. And he was careful about it. And Will had gotten into a random lyft to go to a hotel to meet him, so Will really didn’t have room to talk about being safe.

See, the thing was, was that, it fucking sucked. That was the thing. That was what really rankled. Because he was pretty sure he did have feelings for Will. And all the replies on Reddit were telling him to go for it. And, yeah, maybe he referred to them as fuck buddies, because, well, that’s what they did. He asked Will over and they fucked and then… and then Will cleaned everything up, got him a bottle of water, and cooked him dinner while apparently having a heart to heart with his _cat_. 

So, they were fuck buddies. And he didn’t have multiple fuck buddies, so yes, exclusive fuck buddies.

Well. Okay, chill. They hadn’t defined the relationship, so Will might not be exclusive.

An unbidden image formed in Derek’s mind. Will’s lips dragging over the skin of someone else’s abs. Will’s strong, calloused hands lifting a leg up into position. 

He shook his head. He wasn’t going to do this. That was not helpful. 

It helped to hum _The Song That Never Ends_. 

So, really, the thing was that Derek didn’t know what to make of any of it. He’d never had a fuck buddy or a hookup or even a casual relationship last this long. He’d never had one of those with someone who seemed to care if he was comfortable and, like, nourished or whatever afterward. Fuck, he wasn’t sure if his _friends_ would put in that much effort to make sure he was fed and hydrated. Like, sure, they’d order him some food, but cooking for him? On the regular?

And, Will did ask him over to meet his friends a couple of times. He didn’t pressure him or anything, just, a casual invite. 

He pulled out his phone and started scrolling through their messages. Will hadn’t messaged him anything other than updates about The Contessa either. But there were plenty of messages before that to read through. 

Reading through his fuck buddy’s texts to search for evidence that he was also secretly in love was what Derek’s therapist would call “unhealthy”, but whatever. She wasn’t in Prague.

He probably should have realized sooner when he got back to the messages that weren’t actually from either of them. But it wasn’t until he read a message ostensibly from him that he sat up, eyes wide.

> Yeah, I’m rich, right? So, I like to just travel the world and fuck whoever I feel like, whenever I feel like it.

He closed his eyes. That at least explained why Will had thought that he was going to be sleeping his way through the population of Europe. It wasn’t just some stereotype or biphobia or something. It was his damn friends.

He amended his mental note from thanking them for swiping on Will to being pissed at them.

Then he texted them to let them know he was pissed. Like seriously, what the fuck were they thinking?

He hesitated with this thumb over the message field to send a message to Will. He did need to tell Will that he’d developed feelings. Probably, their arrangement would end because Will wouldn’t be able to deal with the feels. But, he was shit at hiding stuff like that. His mind was already darting off to think about what kind of souvenirs he could get for Will.

> Derek: Yo. Just read back the stuff from the start, when it was our friends. Just so you know, I don’t travel just to have sex. Like, ngl, I’ve hooked up before they swiped on you. But, like you said, since then, exclusive hookups.

It wasn’t sufficient. He should say more. It already felt weird and formal and stiff just texting with proper grammar and spelling (mostly). He scrunched up his face and held his breath for a moment before letting it out in a rush. He had to leave it at that. The rest should be in person. 

Except.

> Derek: It’s chill if not 4 u, tho. Chill.

* * *

He didn’t know what was going on. He hadn’t heard from Derek while he was overseas except to check on The Contessa, and then Derek had returned. Will had taken care to make sure he wasn’t at Derek’s place when he returned, and he’d left the key.

It was just for cat sitting. It wasn’t like Derek had given him the key to his house as like a relationship stage or something like that. And the cat sitting was over. And he’d kind of thought that the casual relationship was probably going to be over too. 

Sure, it made sense that Derek couldn’t bring back a new hookup from Europe. Well, he probably could, actually. But even if he didn’t bring back someone new to take self care breaks with, or whatever, Will had gotten too domestic and had weirded Derek out, probably. 

True, Derek didn’t seem to mind him cooking. And Will was pretty sure there were a lot of times that Derek forgot to eat until Will made him food. 

Whatever. Things had gotten weird because Derek had gone to Europe and as much as Will really wanted to be happy for him and wanted him to be happy however made him happy, it had still hurt to be told “hey, I won’t be hooking up with you, but fear not, I’ll be in Europe with many other wicked interesting people to hook up with.” And then he got relegated to cat sitter. Not even a hook up anymore, just part of the staff. Which was wicked clear when he only got messages about The Contessa.

He looked at his phone again.

> Derek: Hey, wanna come over?

How was he supposed to respond to that? What was he supposed to say?

Were they still hooking up? Was something wrong with The Contessa? 

He frowned at that and tapped out a reply.

> Will: Be over in a few.

> Derek: I can send a lyft

> Will: I’m good. Be there in a few.

When he got to Derek’s house, The Contessa was in her spot on the couch, and she was deliberately ignoring Will. 

“Hey, sweet girl. Don’t you love me anymore?” He rubbed his thumb over the top of her head and she leaned into it. Apparently, she was upset, but not enough to stay mad.

“She missed you. We both did. But I had longer to miss you.” Derek was right behind him. Not just right behind him, but plastering himself to Will’s back as he stood back up.

He took a moment to close his eyes and readjust. Apparently, everything was weird, but fine, and they were just going to go back to whatever they had been doing. He turned in Derek’s arms, and immediately had Derek’s soft, faintly strawberry flavored, lips pressing into his. 

He pulled back a bit and smirked. “If you missed me _that_ much, you could have texted while you were gone.”

“Uh, chill. I did.”

“Texting about your cat doesn’t _really_ count.” He smiled to indicate he was just chirping. It was all fine. It was all just fine.

Instead of continuing the make out and moving it to the bedroom, Derek pulled even further away with a frown. “I did. I texted you and you didn’t reply, so I dropped it.”

Will would definitely have remembered that. He pulled out his phone and scrolled through the messages from Derek. Since he’d left for Europe, the only messages were about The Contessa and the message that night. He handed the phone over to Derek with a shrug. “You didn’t. But it’s fine. It’s chill. You were busy.”

Instead of letting it go and getting back to what he’d clearly asked Will over for, Derek pulled out his own phone. 

“What the fuck Prague. It didn’t. It didn’t freaking send the messages.” He pulled away and rubbed at his temples. “This is mad embarrassing now.”

There wasn’t really anything to say to that, so Will just raised his eyebrows.

“Do you- actually no. Wow, these are mad embarrassing. I just- chill. I just had tried to send you a message saying that idk what my friends were on about when they were messaging your friend that first night, but I don’t travel just to have sex with whoever.” He paused and turned away. “Fuck, this really sounds like I’m just saying shit to get in your pants again.”

“Unnecessarily.”

“What?”

“I told you before you left. I wasn’t trying to like, slut shame you. Like, be happy with whoever makes you happy, or whatever, dude.” 

“Just you.” Derek sighed and let his hand drop. “That’s what I was trying to text you. That, like I haven’t. I know we didn’t talk about it, but sure, we’re fuck buddies, and at least on my side, it’s been exclusive. Even with Europe. So. Idk if you care.”

It made sense, in a way. The reason they’d started hooking up was because Derek’s friends had decided he wouldn’t find someone to hook up with on his own. And, pretty similar for Will’s friends, actually. So, it made sense that Derek hadn’t bothered to find other hookups. 

He stepped in close to Derek, his thumb guiding Derek’s chin until their lips were hovering millimeters apart. “Chill. Exclusive fuck buddies. A whole new thing.”

And then he kissed Derek like Europe had never happened. Like he hadn’t spent weeks trying to reassess his life and figure out where he’d misstepped. Like he really didn’t want the end of that title to be something other than fuck buddies.

And Derek’s hands were in his hair and in his back pocket and it was a little less weird.

* * *

Derek waited. They had a routine, and if Will had been awkward and stiff when he first arrived, it hadn’t lasted long. Not as long as Will had anyway. He smirked a little at his internal joke. He managed to avoid any mid-coital love confessions, which had been more difficult than anticipated. 

So, he waited until Will brought the bottle of water, cold from the fridge, then caught him by the wrist before he could walk away. 

“I was thinking.”

Will paused and looked back at him, eyebrows raised. “Were you now?”

“You don’t have to cook dinner for me.”

Will stilled again, his face seeming to shutter. “Ayuh. Sure thing.”

He had to press through before Will pulled away and left. He couldn’t hold him there, not and say what he was trying to say. “I mean, you never _have_ to cook for me. It’s mad awesome that you do. But, what I meant was. I was thinking, if you wanted to cook for me, you could cook breakfast instead.”

There was a slight pause before Will responded. “Ayuh. I could cook breakfast for dinner. Anything in particular you were craving? Gotta say, if you want something fancy and European, then I hope you got some groceries.”

“I meant breakfast for breakfast. You could stay the night.”

Will looked at him for a long time and Derek didn’t bother trying to hide his feelings. He wanted Will to stay. He’d spent months seeing Will for an evening, a few hours, then weeks without seeing him at all, and it all just really fell short of what he really wanted. Maybe they wouldn’t work as more than fuck buddies. Maybe he was pressing his luck and would break the arrangement that they had, especially after the miscommunications and confusion that had barely been smoothed over earlier in the evening. 

But he wanted Will to stay, to sleep in his bed. 

Will gently pulled his arm from Derek’s grasp and swallowed hard before responding. “I have work in the morning.” 

A few minutes later, he heard the sound of the front door closing.


	5. Chapter 5

Will was back to expecting to never hear from Derek again. He knew he hadn’t handled it well when Derek asked him to stay the night. He knew that he’d probably blown his shot. Any possible shot he’d had to continue the friends with benefits thing or even move it into just a friends kind of situation had been destroyed when he walked out of the house without a word. 

But what was he supposed to say? What was he supposed to do? He couldn’t stay the night. He couldn’t lay beside Derek in that bed and not want it to keep happening. He couldn’t see that as less than not casual. And it had just been a lot for one day. 

So he’d left. He’d walked out and shut the door on the relationship, whatever it was. Because Derek didn’t see them as more than exclusive fuck buddies. Derek wouldn’t see them as more. Even if Derek got caught up in his feelings temporarily, eventually he’d move on. Of course he’d move on. He was just lonely and Will was there. Will was the _easy_ option. 

Will spent the next few weeks working and searching online for queer groups that looked interesting like he should have done from the start. And very especially, not thinking about how much he missed Derek. He didn’t block Derek’s number, but he also set it so that he wouldn’t get notifications. 

He was only successful in distracting himself via Friends Night with Chris and Cait, but on the third one after he’d walked out of Derek’s house, there was a knock on the door. He wasn’t expecting anyone, but when he opened the door with the chain lock engaged, he was definitely not expecting to see Derek standing in the hall, looking shy and unsure of himself. He wasn’t sure he’d ever seen Derek look unsure of himself for more than maybe a second.

He shut the door. 

He opened it again after disengaging the chain lock, then stepped through, shutting it again after him.

“What are you doing here? How’d you even….” He trailed off, looking over Derek, reassuring himself that he was whole and okay. Whatever had brought Derek to his door, it wasn’t a life-threatening injury at least.

“It’s Friends Night, right? You invited me. If that’s chill. I, uh, I brought some wine. I don’t know if you guys drink wine at Friends Night.” He held up a bottle then frowned at it thoughtfully.

“You never came to Friends Night before. Why now?”

“Because I miss you, Will. Okay? I know I pushed too hard, too fast. Asking you to stay the night was a dumb move. But I can be chill, right? I mean, if you aren’t into me like that, it’s chill. But, you did invite me, and then you weren’t replying to my messages. And I can’t just stop loving you, but it can be a friend thing, if you’re into that. So. Ch’yeah.”

Will closed his eyes and took a deep breath. “Don’t say that when you don’t mean it, Derek.”

“I-”

“You don’t love me. You don’t even know me. You’re just, you’re caught up in your feelings or something. And I can’t deal with that, ok? I can't really deal with you building me up to let me down, so, just. I can't. You don't mean it and I can't.”

He turned away before Derek saw how much he’d been affected by it all, and his hand was on the doorknob when Derek reached out to stop him.

“I’ve never meant anything more in my life, Will. I-. I thought about you the whole time I was in Europe. You’re the most caring and gentle person. The way you are with The Contessa. Fuck, the way you are with me. You act like it’s just the expected thing that you’d make sure I was comfortable and cook for me. That’s not typical, Will. And it’s, I mean, you don’t have to, but it’s nice. There’s just. I know that I said that I wouldn’t have swiped on you, but I would have been wrong and I’m really glad my friends did because you’re kind and caring and a good cook and hot and my cat loves you.”

“We don’t even know each other. You can’t love me. Okay. You can’t. Just like I can’t love you. I don’t even know what kind of author you are. You don’t even know I don’t drink alcohol. We don’t know each other.” He set his jaw. Because that was the crux of it all. He couldn’t love Derek and Derek couldn’t love him because they’d never even really been friends. They knew nothing about each other. And just because Derek’s exes were all assholes apparently was even more reason that Will couldn’t take advantage of him being caught up in his feelings.

“Chill. What if, we tried? What if we tried knowing each other? Like, actual proper dating. Not hooking up. Dating.”

The breath that Will let out only shuddered a little and he was damn proud of that. Will knew that Derek didn’t know what he was offering. That he wasn’t trying to hurt Will. He was just caught up in a fantasy, the same one Will had indulged in a few times. Except Will had always known it would never be reality.

“Look, I knew from the start that I’m not the kind of guy that a guy like you takes home to his friends and family, okay? It’s- It’s chill.” 

“If you don’t want to try, I can’t make you. I’ll stop texting. I won’t bother you. But, I think we could be good together. I think we could be friends, and I think we could love each other. I will introduce you to my friends. When are you free? We can go meet my parents right now, but it might require an international flight. I’m not going to beg. But if you think that I’m just saying this because I’m caught up in my feelings-.”

Will couldn’t help the half snort, half laugh that escaped. Derek was being very extreme for someone who was trying to convince him that he was chill and not caught up in his feelings.

“We can take things slow. Can I take you out tomorrow? Or next week? Whenever is good for you.”

Will turned slowly and searched Derek’s face. “You really want to try starting over? Actual dating?”

“Ch’yeah. I think it would be mad perfect, honestly.”

“Okay. You should probably meet Chris and Cait. And you should know that I don’t put out on the first date.”

“Chill. I like a guy with boundaries.”

* * *

The lights slowly turned up, dim at first with a very slow brightening to normal so that everyone’s eyes could adjust. Will wasn’t moving from his seat beside him, so Derek stayed relaxed as well.

“I love the planetarium. Can’t really see the stars in the city, but here we can explore them.” 

“You like the stars, huh?”

“Ch’yeah. They’re like freckles across the sky.”

Will made a soft noise and Derek looked over quizzically.

“Just usually hear that the other way around. Freckles like constellations or some sh-, thing.”

“I guess it depends on what your point of view is. Which you think is the metric for the other to be compared.” He reached out and brushed his fingertips over Will’s cheek.

“Seriously? You been practicing that line?”

“Hey, chill.” He couldn’t help the smile though. “Yeah, actually, for weeks. Did it work?”

“It was pretty good.” Will gave him a small smile then turned to look around the theater. “Looks like most everyone’s out. Did you want to look at the rest of the museum, or are we only here for sky freckles?”

“Sky freckles. Name of my next book.”

“Maybe if you write children’s books.”

“Oh, uh.” He focused on his feet on the stairs for a few moments. In theory, he was trying to avoid tripping and falling. In reality, he was doing that and also bracing with some extra chill. “Poetry actually. I’m a poet. I write poetry.”

Will was quiet until they reached the bottom of the stairs and headed out of the planetarium. “Ayuh. Works for a poetry book, too.”

He turned away to avoid letting Will see him being unchill about that, and cleared his throat. “Chill. We can look through the rest of the museum if you want. You ever been here before?”

“No. Only vicariously through Night At The Museum.”

“Like that movie, huh?”

“Octavius and Jedediah were in love. It was a good story.”

Derek stared at him in shock for a moment. “Chill. I don’t think I’d have guessed that you were a Jedtavius shipper.”

“Is it shipping when Jedediah canonically said ‘I ain’t quiitin’ you’ to Octavius?”

“Ye-” Derek broke off as Will’s fingers laced through his own. He took a deep breath, then another. After the fifth breath when his heart rate hadn’t slowed down, he gently pulled his hand away. “Um. Sorry. We can’t do that.”

“Right. Right. I get it.” Will nodded and shoved his hands into his pockets, only the slightest tightness around his eyes and the corners of his mouth giving away that he wasn’t chill.

“I mean, I want to. But I’ll make a scene because it’s, uh, chill, right? Like, it’s mad chill. It’s-” He broke off again because Will took his hand again.

“If the only problem is you making a scene, I can live with that. Jedediah wasn’t my favorite for nothing.”

Derek swallowed with a smile. “Sometimes, Jedediah doesn’t want to make Octavius uncomfortable.”

Somehow, he managed to keep his chill and not make a huge scene about the fact that Will continued to hold his hand through the entire museum. He kept his chill through dinner, and all the way until they were standing outside of Will’s apartment. 

Will’s lips were softer than he remembered as they parted under his own, but his hands were just as firm and steady on Derek’s hips. But they were taking things slow this time, so Derek pulled away much sooner than he would have preferred. 

“Can I take you out again next week?”

“No.”

Derek’s heart skipped a beat as he tried to figure out what had changed between the hand holding and the kissing and now to make Will not want to see him again. 

“But I’d like to take you out, if that’s okay.”

“Oh. Ch’yeah. That’s chill. That’s mad chill.” He took a deep breath. “Full disclosure, since we’re doing that communicating thing. You scared me there.”

Will’s hand wrapped around to the back of his neck and pulled him in until their lips were pressed together again and Will’s tongue swept gently across his lips. When Will pulled away again, he gave Derek a small smile. “Sorry for scaring you. I, uh. I like you. A lot. And I do want this to work. And, uh. I can’t-.” 

Will stopped and took a couple of deep breaths, so Derek rubbed their noses together. A reminder that he was there and wanted the same thing. 

“I need us to be, like, equal partners in this. I need to take you out sometimes, too. Not just you taking me out.”

“That’s chill. I’d like that. As long as I get to see you again. And I think I still owe your friends a double date in a helicopter, so that’s at least two more dates, right?”

“Ayuh. That’s. Actually, I was thinking. I, uh. I have some vacation time coming up in a couple of months. I was planning to go back home for a week. And, uh, yeah. If you want, if we’re still, uh, doing this. It would be wicked nice if you wanted to go with me.”

Derek froze again, though his heart missed a beat for an entirely different reason this time. “You want me to go to Maine with you?”

“Ayuh. We’ve got real sky freckles up there.”

“You want me to meet your family?”

“That’s-. Yeah. They’d be there. That would be part of it.”

He pressed their lips together again as soon as Will stopped talking. “Ch’yeah. Yes. That’d be-. That’d be great. Mad nice. Ch’yeah.” 

“Cool. Um. We should, you know, stop making out in the hallway.”

“Ch’yeah.” Derek pressed another kiss to Will’s jaw. 

“And I should go into my apartment.”

“Ch’yeah.” Another kiss, further back than the last.

“And you should probably, go home.”

“Ch’yeah. I should go home.” He pressed one last kiss at the joint of Will’s jaw. 

“And text me.”

“And text you.”

“And I’ll take you out next week.”

“Ch’yeah. You will.” 

He grinned at Will, who was blushing faintly as he reached behind himself to open the door and flashed a smile before he disappeared.


End file.
